JPS61185569A - Purification of water-soluble dye - Google Patents
Purification of water-soluble dyeInfo
- Publication number
- JPS61185569A JPS61185569A JP2566385A JP2566385A JPS61185569A JP S61185569 A JPS61185569 A JP S61185569A JP 2566385 A JP2566385 A JP 2566385A JP 2566385 A JP2566385 A JP 2566385A JP S61185569 A JPS61185569 A JP S61185569A
- Authority
- JP
- Japan
- Prior art keywords
- water
- soluble dye
- dye
- ammonium
- aqueous solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000746 purification Methods 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 38
- 238000005185 salting out Methods 0.000 claims description 19
- 239000007864 aqueous solution Substances 0.000 claims description 18
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 11
- 239000001099 ammonium carbonate Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 9
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 7
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 14
- 239000007787 solid Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000003863 ammonium salts Chemical class 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 241000283986 Lepus Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- -1 capro2cutam Chemical compound 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は水溶性染料の精製法に関するものである。[Detailed description of the invention] [Industrial application field] The present invention relates to a method for purifying water-soluble dyes.
水溶性染料の合成は通常、水溶媒で行なわれるため、得
られる反応混合物は水溶性染料の水浴液となる。そして
、ここで得られる水溶液中には、副生物や反応に使用し
た塩等が含有されている。従って、目的とする水溶性染
料と、反応混合物中に存在する副生物や塩などを分離す
る必要があり、そのためには通常、この反応水溶液な塩
析等の処理によって目的とする水溶性染料を精製するこ
ととなる。Since the synthesis of water-soluble dyes is usually carried out in an aqueous solvent, the resulting reaction mixture is a water bath solution of the water-soluble dye. The aqueous solution obtained here contains by-products, salts used in the reaction, and the like. Therefore, it is necessary to separate the desired water-soluble dye from by-products, salts, etc. present in the reaction mixture, and for this purpose, the desired water-soluble dye is usually separated by salting out the reaction aqueous solution. It will be refined.
しかし、この塩析によって得られる水溶性染料は、塩析
に用いた多量の塩を含有するため、この塩析水溶性染料
を水に溶解した場合、含有される塩の影響によυ高濃度
の染料水溶液が得られないという欠点があった。However, the water-soluble dye obtained by this salting-out process contains a large amount of salt used in the salting-out process, so when this salting-out water-soluble dye is dissolved in water, the concentration of The disadvantage was that it was not possible to obtain an aqueous dye solution.
すなわち、本発明の要旨は、水溶性染料水溶液に、炭酸
アンモニウム、重炭酸アンモニウム又ハカルバミン酸ア
ンモニウムを添加し、水溶性染料を塩析し、塩析混合物
をろ別し、得られたケーキを水性媒体に溶解又は懸濁し
、次いで該溶解液又は懸濁液をｌＩｏ℃以上の温度下に
ｏ、ｒ時間以上保持することを特徴とする水溶性染料の
精製法に存する。That is, the gist of the present invention is to add ammonium carbonate, ammonium bicarbonate, or ammonium hacarbamate to an aqueous solution of a water-soluble dye, salt out the water-soluble dye, filter the salting-out mixture, and divide the resulting cake into an aqueous solution. A method for purifying a water-soluble dye, which comprises dissolving or suspending the dye in a medium, and then maintaining the solution or suspension at a temperature of 10° C. or higher for a period of o, r or more.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明の水溶性染料としては、特に限定されるものでな
いが、通常、水溶性基としてスルホン酸塩基、又はカル
ボン酸塩基を含有する公知の染料を挙げることができ、
例えば次表ＣＡ）に示す水溶性染料等が使用可能である
。The water-soluble dye of the present invention is not particularly limited, but can include known dyes that usually contain a sulfonic acid group or a carboxylic acid group as a water-soluble group,
For example, water-soluble dyes shown in Table CA) below can be used.
表［Ａ）
本発明では通常、合成反応によシ得られた前記染料を含
む反応混合物が用いられる。Table [A] In the present invention, a reaction mixture containing the dye obtained by a synthetic reaction is usually used.
本発明は、上述の水溶性染料の水溶液を塩析するに当シ
、塩として炭酸アンモニウム、重炭酸アンモニウム又は
カルバミン酸アンモニウムを用いることを必須の要件と
するものである。The present invention requires the use of ammonium carbonate, ammonium bicarbonate, or ammonium carbamate as the salt when salting out the aqueous solution of the water-soluble dye described above.
ここで用いる塩は水溶性染料を実質的に全て塩析出来る
童以上であれば良い。この塩は通常固体状又は溶解液の
形で直接混合物に添加されるが、場合により、例えば炭
酸ガスとアンモニアを反応混合物に供給することによシ
系内で前記塩を生成させても良い。塩析後、混合物は通
常、濾過により水溶性染料のケーキを回収するが、この
ケーキ中には水溶性染料とともに塩析のために加えた塩
も含有されることになる。また、との塩析により水溶性
染料の対イオンの大部分はアンモニウム塩に変化する。The salt used here may be any salt or salt which can salt out substantially all of the water-soluble dye. The salt is usually added directly to the mixture in solid or dissolved form, but optionally it may also be formed in the system, for example by feeding carbon dioxide and ammonia to the reaction mixture. After salting out, the mixture is usually filtered to recover a cake of water-soluble dye, which contains the water-soluble dye as well as the salt added for salting out. Furthermore, most of the counter ions of the water-soluble dye are changed into ammonium salts by salting out with.
本発明は塩析によシ回収した未乾燥の湿ケーキを水性媒
体に溶解又は懸濁させ、１７０℃以上、好ましくは３０
℃〜１００℃の温度でｏ、ｓ時間以上、好ましくは２〜
２０時間保持することで溶解又は懸濁した水溶液中のア
ンモニウム塩を熱分解させることが必要である。In the present invention, the undried wet cake recovered by salting out is dissolved or suspended in an aqueous medium, and
o, s or more at a temperature of ℃ to 100℃, preferably 2 to
It is necessary to thermally decompose the dissolved or suspended ammonium salt in the aqueous solution by holding it for 20 hours.
この処理において処理温度があまシ低い場合又は処理時
間があまシ短かい場合には上述の工程で加えたアンモニ
ウム塩の分解が不十分であり、低い塩濃度の染料水溶液
を得ることができない。In this treatment, if the treatment temperature is too low or the treatment time is too short, the decomposition of the ammonium salt added in the above-mentioned step will be insufficient, making it impossible to obtain an aqueous dye solution with a low salt concentration.
この処理に用いる水性媒体の使用量は少なくとも染料ケ
ーキを分散できる程度の量が必要であり、通常、湿ケー
キに対して０．３〜１０重量倍、好ましくは０．５〜３
重量倍である。The amount of aqueous medium used in this treatment must be at least enough to disperse the dye cake, and is usually 0.3 to 10 times the weight of the wet cake, preferably 0.5 to 3 times the weight of the wet cake.
It is twice the weight.
この時に使用する水性媒体としては通常、水又は例えば
、尿素、カプロ２クタム、エチレングリコール及びトリ
エタノールアミンの様な溶解促進剤を含有する水溶液で
ある。また、この熱分解処理は通常常圧下で行なうが、
場合によっては減圧下で実施しても良い。The aqueous medium used here is usually water or an aqueous solution containing a solubility promoter, such as urea, capro2cutam, ethylene glycol and triethanolamine. In addition, this thermal decomposition treatment is usually carried out under normal pressure,
Depending on the case, it may be carried out under reduced pressure.
なお、この処理はアンモニウム塩が熱分解し、炭酸ガス
及びアンモニアガスなどのガスが発生するので、これら
の発生ガスの処理装置を備えた攪拌槽で実施するのが好
ましい。In addition, since this treatment thermally decomposes the ammonium salt and generates gases such as carbon dioxide gas and ammonia gas, it is preferable to carry out the treatment in a stirring tank equipped with a processing device for these generated gases.
一
上述の様譚して得た水溶性染料の水溶液はそのまま高濃
度染料水溶液としても使用されるがその目的に応じて後
処理される。例えば、水量が多い場合には蒸発濃縮する
か、又は一旦、スプレー乾燥し、これを再溶解すること
によシ、所望濃度の水溶性染料の水溶液を得ることが出
来る。また、スプレー乾燥により得られた染料粉末はそ
の１１粉末品として商品化することも出来る。いずれの
場合においても本発明では無機塩の含有量が少ないので
高濃度の水溶性染料を得ることが可能である。The aqueous solution of water-soluble dye obtained in the above-mentioned manner can be used as a high-concentration dye aqueous solution as it is, but is post-treated depending on the purpose. For example, if the amount of water is large, an aqueous solution of a water-soluble dye with a desired concentration can be obtained by evaporating and concentrating it or by spray drying it and redissolving it. Moreover, the dye powder obtained by spray drying can also be commercialized as the 11 powder product. In any case, in the present invention, since the content of inorganic salt is small, it is possible to obtain a highly concentrated water-soluble dye.
本発明の処理によれば、塩析工程で加えた炭酸アンモニ
ウム、重炭酸アンモニウム又はカルバミン酸アンモニウ
ムが熱分解され、これらの無機塩が除去されるため、染
料の水に対する溶解度が向上し、高濃度化が可能な染料
水溶液が得られる。According to the process of the present invention, ammonium carbonate, ammonium bicarbonate, or ammonium carbamate added in the salting out process is thermally decomposed and these inorganic salts are removed, so that the solubility of the dye in water is improved and a high concentration is obtained. An aqueous dye solution is obtained that can be oxidized.
以下、本発明を実施例により更に詳細に説明するが、本
発明は、以下の実施例に限定されるものではない。EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples.
実施例／
カップリング反応によシ得た下記構造式ＣＩ）で示され
る本発明の水溶性染料を含む反応液１０００ｒｔＬｌ（
固形分６．クチ、固形物中のＮａＣ！１含量ａ６％）に
、ｌＩＯ℃の温度で重炭酸アンモニウム／’７０７／を
攪拌下、７時間かけて徐々に加え塩析を行った。Example/1000rtLl of a reaction solution containing the water-soluble dye of the present invention represented by the following structural formula CI) obtained by a coupling reaction.
Solid content6. Mouth, NaC in solid food! Ammonium bicarbonate/'707/ was gradually added over 7 hours under stirring at a temperature of 1IO° C. to perform salting out.
・・・・・・・〔１〕
次いで、塩析後の混合物をｅ過し、回収した湿ケーキ−
７０１！（固形分３０％、固形物中のＭａｉｌ含ｉｉ＆
％、固形物中の重炭酸アンモニウム含量ｌＩ３％）を水
ＪコθＮに懸濁させ、６５℃の温度で３時間熱処理を行
った。得られた水溶液（ｌＩ＆ＯｍＪ）中のアンモニウ
ム塩量を測定したところ第１表に示す様な結果を得た。...... [1] Next, the mixture after salting out was filtered, and the collected wet cake was
701! (Solid content: 30%, including Mail in the solids)
%, ammonium bicarbonate content in solid matter 1I 3%) was suspended in water and heat treated at a temperature of 65° C. for 3 hours. When the amount of ammonium salt in the obtained aqueous solution (lI & OmJ) was measured, the results shown in Table 1 were obtained.
実施例２〜３
実施例／の方法において熱処理の条件を第１表に示すよ
りに変化させた場合の結果を第１表に示す。Examples 2 to 3 Table 1 shows the results when the heat treatment conditions were changed from those shown in Table 1 in the method of Example//.
実施例ダ
実施例／の方法において、熱処理を尿素３６１１カプロ
ラクタムｌＯｇ及びトリエタノールアミン／コｙを加え
た水溶液３！Ｏｒｄ中で７０℃の温度で３時間実施した
場合の結果を第１表に示す。なお、この染料水溶液は０
℃に冷やしても結晶の析出はなく安定であった。In the method of Example/Example, heat treatment was performed using an aqueous solution containing 3611 urea, 10 g of caprolactam, and triethanolamine/coy. The results are shown in Table 1 when the test was carried out at a temperature of 70° C. for 3 hours in Ord. Note that this dye aqueous solution has 0
Even when cooled to ℃, there was no precipitation of crystals and the product remained stable.
実施例よ
縮合反応により得られた下記構造式〔…〕で示される湿
ケーキ１ｏ０１１（固形分１］、固形物中のＭａｉｌ含
量３２％）ｆ６０℃温水ｇｏ。Example Wet cake 1o011 (solid content: 1, Mail content in the solid: 32%) represented by the following structural formula [...] obtained by condensation reaction f 60°C hot water go.
属に溶解させ、弘０°Ｃの温度でｓｋ酸アンモニウム７
２ｔ１を攪拌下、３０分かけて徐々に加え塩析を行った
。ammonium skate at a temperature of 0°C.
2t1 was gradually added over 30 minutes with stirring to perform salting out.
次いで、塩析後の混合物をｆ過し、回収した湿ケーキ／
２０ｇ（固形分３３％、固形物中のＭａｉｌ含量ｕ、ｒ
％、固形物中の重炭酸アンモニウム含ｘ、ｉｏ、ｏ優）
を水λダＯプに懸濁させ、６０℃の温度で６時間熱処理
を行った。得られた水溶液（Ｊ ｏ ｏｍｌ）中のアン
モニウム塩量を測定したところ第２表に示す様な結果を
得た。Then, the mixture after salting out was filtered, and the collected wet cake/
20g (solid content 33%, Mail content in solids u, r
%, ammonium bicarbonate content in solids x, io, o)
was suspended in water and heat treated at a temperature of 60° C. for 6 hours. When the amount of ammonium salt in the obtained aqueous solution (J oml) was measured, the results shown in Table 2 were obtained.
また、この水溶液に尿素２７１１．ト’）エタノールア
ミン／／１１エチレングリコールコＪ、Ｆを加え、７０
′Ｃで１００朋Ｈ，９の真空度で−ざＱ−まで蒸発濃縮
した。この溶液の染料固形分はＩＯ係で完全に溶解して
おり、ｏ’６まで冷却しても結晶の析出はなく安定であ
った。In addition, urea 2711. g') Add ethanolamine//11 ethylene glycol CoJ, F, 70
The mixture was concentrated by evaporation at 100°C and a vacuum of 9°C to -Q-. The dye solid content of this solution was completely dissolved in the IO ratio, and the solution remained stable without precipitation of crystals even when cooled to o'6.
比較例１
実施例夕において、塩析により回収した湿ケーキを懸濁
させた水溶液の熱処理条件な２０℃の温度で３時間処理
した後のアンモニウム塩量を測定したところ第、２表に
示す様な結果を得た。Comparative Example 1 In the evening of the example, the amount of ammonium salt was measured after the aqueous solution in which the wet cake recovered by salting out was suspended was treated at a temperature of 20° C. for 3 hours, as shown in Table 2. I got good results.
比較例コ
比較例／と同じ水溶液を５０℃の温度で０．２Ｓ時間（
７３分間）熱処理した後のアンモニウム塩量を測定した
ところ第２表に示す様な結果を得た。Comparative Example The same aqueous solution as Comparative Example/ was heated at a temperature of 50°C for 0.2 S hours (
The amount of ammonium salt after heat treatment (73 minutes) was measured, and the results shown in Table 2 were obtained.
第１表
第ａ表
〔発明の効果〕
本発明によれば、塩析により回収した水溶性染料の湿ケ
ーキを乾燥することなく、そのまま水中に分散又は溶解
して熱処理することによシ、容易に水溶液中の無機塩含
有量を低下させることができる。したがって、本発明は
操作が簡単である上、脱塩の九めのエネルギーコストも
低く、工業的に極めて価値のある方法である。Table 1 Table a [Effects of the Invention] According to the present invention, a wet cake of water-soluble dye recovered by salting out can be easily dispersed or dissolved in water without drying and heat-treated. The content of inorganic salts in aqueous solutions can be reduced. Therefore, the present invention is not only easy to operate, but also has low energy costs for desalination, making it an industrially extremely valuable method.
出 願 人 三菱化成工業株式会社 代 理 人 弁理士 長谷用 − （ほか７名）Sender: Mitsubishi Chemical Industries, Ltd. Representative Patent Attorney Hase - (7 others)
Claims (1)
アンモニウム又はカルバミン酸アンモニウムを添加し、
水溶性染料を塩析し、塩析混合物をろ別し、得られたケ
ーキを水性媒体に溶解又は懸濁し、次いで該溶解液又は
懸濁液を４０℃以上の温度下に０．５時間以上保持する
ことを特徴とする水溶性染料の精製法。(1) Adding ammonium carbonate, ammonium bicarbonate or ammonium carbamate to the water-soluble dye aqueous solution,
Salting out the water-soluble dye, filtering the salting out mixture, dissolving or suspending the resulting cake in an aqueous medium, and then heating the solution or suspension at a temperature of 40°C or higher for 0.5 hours or more. A method for purifying water-soluble dyes characterized by the retention of water-soluble dyes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2566385A JPS61185569A (en) | 1985-02-13 | 1985-02-13 | Purification of water-soluble dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2566385A JPS61185569A (en) | 1985-02-13 | 1985-02-13 | Purification of water-soluble dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61185569A true JPS61185569A (en) | 1986-08-19 |
Family
ID=12172035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2566385A Pending JPS61185569A (en) | 1985-02-13 | 1985-02-13 | Purification of water-soluble dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61185569A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100355097B1 (en) * | 2000-05-13 | 2002-10-11 | 주식회사 이스트웰 | The stabilizing method of coloring dyes for pulp |
| US7246726B2 (en) | 2001-10-25 | 2007-07-24 | Musashi Engineering, Inc. | Liquid material delivering method and device therefor |
| US7735695B2 (en) | 2001-10-17 | 2010-06-15 | Musashi Engineering, Inc. | Liquid material delivering method and device therefor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS572366A (en) * | 1980-05-03 | 1982-01-07 | Bayer Ag | Manufacture of low salt content water-soluble dye |
-
1985
- 1985-02-13 JP JP2566385A patent/JPS61185569A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS572366A (en) * | 1980-05-03 | 1982-01-07 | Bayer Ag | Manufacture of low salt content water-soluble dye |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100355097B1 (en) * | 2000-05-13 | 2002-10-11 | 주식회사 이스트웰 | The stabilizing method of coloring dyes for pulp |
| US7735695B2 (en) | 2001-10-17 | 2010-06-15 | Musashi Engineering, Inc. | Liquid material delivering method and device therefor |
| US7246726B2 (en) | 2001-10-25 | 2007-07-24 | Musashi Engineering, Inc. | Liquid material delivering method and device therefor |
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